“Undoing Sex: against sexual optimism” is a critique of sex-positivity that both draws upon and completely transcends second-wave feminist critiques. The essay explores the metaphysical quandaries faced by the “not-man” in their engagement with and survival of sex. Centering sex negativity in a transgender, queer experience of how the image of sexual pleasure and health is produced, marketed, and consumed by people of all genders, the text brings Marx, Foucault, Afropessimism, and other currently useful theories to bear upon the sexual impasse many (all?) of us face. It offers no prescriptive conclusions, but rather to speaks an array of inadequate coping strategies. We recommend it for all those who choose to have sex, for all those who choose to not have sex, and for those who feel that “choice” is not an adequate word.